✍🏽 Landon’s Loop #146

This week’s newsletter is supported by 1440 & University of Chicago Graham School

What’s in the Loop:

🎙️ Chicago Futurist Vol. 7 with Lewis Burik, Co-Founder & CEO of DubClub

🤖 This Week’s AI Meetup at Drive Capital

📅 7 Events in Chicago This Week

🎙️ Chicago Futurist: Lewis Burik, Co-Founder & CEO of DubClub

After time in the Bay Area, Chicago native Lewis “Lew” Burik returned back home to Chicago to build something special: DubClub.

DubClub started as a solution to a problem he had as a recreational bettor and has quietly grown into a destination where expert sports bettors and fans win more together. Over four years in, his company has processed over $95M in GMV. A lifelong Chicago sports diehard, Lew now builds close to his users and far from the noise.

Here’s our conversation:

DubClub started as a solution to your own problem as a recreational bettor. At what point did you realize this wasn’t just a tool but infrastructure for an entirely new creator economy?

LB: The marketplace and the economic exchange of value between cappers and fans existed long before DubClub, but the infrastructure was never designed for this esoteric use case. It was always our belief that if we built a great product experience, cappers and fans would want to meet and exchange value using a product that was actually specifically built for them. 

I won’t point to a specific operational or product metric. At DubClub, we expect highly critical thinking regarding the optimal revenue model and cost structure for the business. It is human nature to let costs bloat, and to get complacent on revenue generation. Complacency is the enemy of what we want to build.

Sports betting is polarizing. How do you balance long-term responsibility with short-term revenue, especially when regulation influences product decisions earlier than people expect?

LB: This is a mission-driven and highly ambitious company. Our mission is to build the destination where cappers and fans Win More Together. Decision-making starts and ends with what serves that mission. Because we are profitable and we love our work, we are comfortable making decisions with a long-term, mission-first orientation. We don’t need to optimize decision-making for short-term revenue.

DubClub’s original product vision was to build a self-driving sports betting experience. Think copy trading for sports betting. That was a monster regulatory ball of wax, so we pivoted to the premium content subscription marketplace model. That’s proven to be a wise bet thus far, and is a perfect example of how we think about serving customer needs while remaining compliant and on the right side of regulatory changes.

In marketplaces, a few creators drive most of the volume. How do you avoid their incentives distorting the rest of the ecosystem, and what did you learn about discovery that changed how fans find the right capper?

LB: Success leaves clues. We study top creators and seek to apply what makes them successful to our product experience as a whole.

There is an incredible diversity of what fans are looking for when they purchase a subscription from a capper. Do fans like betting player props or more traditional sides and totals? Does the fan live in a state where only daily fantasy apps are permitted, or do they have access to traditional online sportsbooks? Does the fan want a capper that runs an engaging community experience that complements their plays? These are only a few of the many variables that define which capper is the best fit for any given fan.

Understanding what those preference segments are, and creating an experience that makes discovery in this specific niche effortless is no small task. Because we specialize in sports, and have such depth in our supply of great cappers, we are uniquely well positioned to help a fan find the right capper for them.

Chicago is a sports town. How much has building in Chicago helped shape the product and vision, and what turned out to be DubClub’s first defensible advantage that competitors couldn’t easily copy?

LB: We love being in the mix with actual DubClub users: cappers and fans alike. Chicago is the ideal city to make those moments of planned and serendipitous company + customer interactions happen regularly. We have a steady stream of cappers swinging by our office to meet the team, share ideas, and shoot content. That is an enormous benefit as we move the product forward.

Vertical integration of a very specific end-market was our first defensible advantage. Our exclusive focus on building the destination where cappers and fans Win More Together allowed us to build a product experience, network, and internal set of expertise that competitors couldn’t easily copy.

Prediction markets are gaining visibility and credibility. How do you think about their role alongside creator driven capping / where does DubClub clearly fit versus where it intentionally does not?

LB: Prediction markets offer cappers and fans another venue to access liquidity, compare odds, and tap in to new user promotions. That is a net positive for the ecosystem. These markets have some benefits, and some drawbacks vs. traditional sports books and DFS apps. As new entrants continue to compete for the same users, DubClub will play an important role in routing users towards the venue that sets them up to win more.

What does DubClub look like in 10 years?

LB: We are the destination where cappers and fans Win More Together. We have played a central role in increasing the percentage of sports bettors that are actually long-term winners (currently ~3% of all bettors), and we are the super-app where regular bettors complete their daily workflows.

DubClub is hiring for a number of technical roles in Chicago, including Full Stack Senior Software Engineers and Staff Software Engineers

🎓 Your Path Forward Starts Here

With applications closing soon, now is the time to take the next step toward graduate study through the University of Chicago’s Graduate Student-at-Large (GSAL) and Graduate Student-at-Large: Business (GSALB) bridge programs. GSAL offers a flexible, goal-driven pathway to explore a discipline, build academic credentials, and prepare for advanced study or career transitions

Through GSAL and GSALB, students have gone on to master’s and doctoral programs across the humanities, social sciences, and biological sciences, as well as MBA programs at top schools including UChicago Booth School of Business.

You’ll join more than 10,000 GSAL alumni across major industries around the world, and gain access to a robust network of UChicago students, alumni, and instructional staff.

“The GSAL program has been so fantastic for me because it’s allowed me to grow—not just academically but also personally and professionally.”

Charles Mudd, GSAL alum

Program Benefits:

  • Receive personalized academic advising and academic support

  • Receive formal grades and official transcripts

  • Gain exposure and access to esteemed UChicago faculty, including the potential for references and letters of
    recommendation

  • Take part in networking opportunities with influential professionals.

Application Deadline: March 3, 2026

If graduate study is on your horizon, now is the time to take the next step. Start your application now to be considered for admission to the Spring 2026 quarter.

📅 Who’s Hosting This Week

AI Tinkerers Chicago Feb Meetup ft. DubClub

  • Tuesday

  • Hosted by Drive Capital and DubClub

Chicago Data Night: Philip Rathle (Neo4j)

  • Wednesday

  • Hosted by Drive Capital and UChicago Data Science Institute

Chicago Grassroots Tech Community Meetup

Campus 1871

The New Commerce Creative Stack: AI Video, Influencers, and Shoppable Experiences

YC Visits UChicago

The Liquidity Series: How to Raise, Scale & Sell for Millions

🗞 Previous Newsletters:

👋 See you next week!

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